I've also spent a LOT of time in the startup & venture capital space. Here are a few of the books I've found most insightful.
Got something to recommend? Drop me a note:

OVERVIEW
If Silicon Valley is the greatest wealth-generating machine in the world, Sand Hill Road is its humming engine. That's where you'll find the biggest names in venture capital, including famed VC firm Andreessen Horowitz, where lawyer-turned-entrepreneur-turned-VC Scott Kupor serves as managing partner.
Whether you're trying to get a new company off the ground or scale an existing business to the next level, you need to understand how VCs think. In Secrets of Sand Hill Road, Kupor explains exactly how VCs decide where and how much to invest, and how entrepreneurs can get the best possible deal and make the most of their relationships with VCs. Kupor explains, for instance:
• Why most VCs typically invest in only one startup in a given business category.
• Why the skill you need most when raising venture capital is the ability to tell a compelling story.
• How to handle a "down round," when startups have to raise funds at a lower valuation than in the previous round.
• What to do when VCs get too entangled in the day-to-day operations of the business.
• Why you need to build relationships with potential acquirers long before you decide to sell.
--- Amazon
OVERVIEW
Innovations rarely come from “experts.” Elon Musk was not an “electric car person” before he started Tesla. When it comes to improbable innovations, a legendary tech VC told Sebastian Mallaby, the future cannot be predicted, it can only be discovered. It is the nature of the venture-capital game that most attempts at discovery fail, but a very few succeed at such a scale that they more than make up for everything else. That extreme ratio of success and failure is the power law that drives the VC business, all of Silicon Valley, the wider tech sector, and, by extension, the world.
In The Power Law, Sebastian Mallaby has parlayed unprecedented access to the most celebrated venture capitalists of all time—the key figures at Sequoia, Kleiner Perkins, Accel, Benchmark, and Andreessen Horowitz, as well as Chinese partnerships such as Qiming and Capital Today—into a riveting blend of storytelling and analysis that unfurls the history of tech incubation, in the Valley and ultimately worldwide. We learn the unvarnished truth, often for the first time, about some of the most iconic triumphs and infamous disasters in Valley history, from the comedy of errors at the birth of Apple to the avalanche of venture money that fostered hubris at WeWork and Uber. --- Amazon
OVERVIEW
How do venture capital deals come together? This is one of the most frequent questions asked by each generation of new entrepreneurs. Surprisingly, there is little reliable information on the subject. No one understands this better than Brad Feld and Jason Mendelson. The founders and driving force behind the Foundry Group―a venture capital firm focused on investing in early-stage information technology companies―Brad and Jason have been involved in hundreds of venture capital financings. Their investments range from small startups to large Series A venture financing rounds. The new edition of Venture Deals continues to show fledgling entrepreneurs the inner-workings of the VC process, from the venture capital term sheet and effective negotiating strategies to the initial seed and the later stages of development.
Fully updated to reflect the intricacies of startups and entrepreneurship in today's dynamic economic environment, this new edition includes revisions and updates to coverage on negotiating, gender issues, ICO’s, and economic terms. New chapters examine legal and procedural considerations relevant to fundraising, bank debt, equity and convertible debt, how to hire an investment banker to sell a company, and more.
--- Amazon
OVERVIEW
As Calacanis makes clear, you can get rich―even if you came from humble beginnings (his dad was a bartender, his mom a nurse), didn’t go to the right schools, and weren’t a top student. The trick is learning how angel investors think. Calacanis takes you inside the minds of these successful moneymen, helping you understand how they prioritize and make the decisions that have resulted in phenomenal profits. He guides you step by step through the process, revealing how leading investors evaluate early-stage companies, calculating the risks and rewards, and explains how the best startups leverage relationships with angel investors for the best results. --- Amazon
OVERVIEW
Ali Tamaseb has spent thousands of hours manually amassing what may be the largest dataset ever collected on startups, comparing billion-dollar startups with those that failed to become one—30,000 data points on nearly every factor: number of competitors, market size, the founder’s age, his or her university’s ranking, quality of investors, fundraising time, and many, many more. And what he found looked far different than expected. Just to mention a few:
You will also hear the stories of the early days of billion-dollar startups first-hand. The book includes exclusive interviews with the founders/investors of Zoom, Instacart, PayPal, Nest, Github, Flatiron Health, Kite Pharma, Facebook, Stripe, Airbnb, YouTube, LinkedIn, Lyft, DoorDash, Coinbase, and Square, venture capital investors like Elad Gil, Peter Thiel, Alfred Lin from Sequoia Capital and Keith Rabois of Founders Fund, as well as previously untold stories about the early days of ByteDance (TikTok), WhatsApp, Dropbox, Discord, DiDi, Flipkart, Instagram, Careem, Peloton, and SpaceX. --- Amazon
OVERVIEW
While many people talk about how great it is to start a business, very few are honest about how difficult entrepreneurship is when it comes to running one. Ben Horowitz analyzes the problems that confront leaders every day, sharing the insights he’s gained developing, managing, selling, buying, investing in, and supervising technology companies. A lifelong rap fanatic, he amplifies business lessons with lyrics from his favorite songs, telling it straight about everything from firing friends to poaching competitors, cultivating and sustaining a CEO mentality to knowing the right time to cash in.
Filled with his trademark humor and straight talk, The Hard Thing About Hard Things is an invaluable management book for veteran entrepreneurs as well as those aspiring to their own new ventures, drawing from Horowitz's personal and often humbling experiences. --- Amazon
OVERVIEW
The foremost authority on innovation and growth presents a path-breaking book every company needs to transform innovation from a game of chance to one in which they develop products and services customers not only want to buy, but are willing to pay premium prices for.
How do companies know how to grow? How can they create products that they are sure customers want to buy? Can innovation be more than a game of hit and miss? Harvard Business School professor Clayton Christensen has the answer. A generation ago, Christensen revolutionized business with his groundbreaking theory of disruptive innovation. Now, he goes further, offering powerful new insights.
After years of research, Christensen and his co-authors have come to one critical conclusion: our long held maxim--that understanding the customer is the crux of innovation--is wrong. Customers don't buy products or services; they "hire" them to do a job. Understanding customers does not drive innovation success, he argues. Understanding customer jobs does. The "Jobs to Be Done" approach can be seen in some of the world's most respected companies and fast-growing startups, including Amazon, Intuit, Uber, Airbnb, and Chobani yogurt, to name just a few. But this book is not about celebrating these successes--it's about predicting new ones. --- Amazon
OVERVIEW
In Lead Upwards: How Startup Joiners Can Impact New Ventures, Build Amazing Careers, and Inspire Great Teams, startup marketing leader Sarah E. Brown delivers an illuminating and accessible guide to maximizing your impact and delivering results in a startup leadership role. The author draws on over a decade of experience scaling SaaS companies as she explains how to prepare for, earn, and succeed in an executive role at a startup company.
The book describes every step on the way to realizing your goals―and the goals of your startup―as you navigate the gap between a management role and the executive team. It covers what to do in your first 90 days, how to build and sustain a healthy team culture, and the art of communicating results to your leadership team and board. You’ll also learn:
OVERVIEW
What do you do when you're faced with a big decision? If you're like most people, you probably make a pro and con list, spend a lot of time obsessing about decisions that didn't work out, get caught in analysis paralysis, endlessly seek other people's opinions to find just that little bit of extra information that might make you sure, and finally go with your gut.
What if there was a better way to make quality decisions so you can think clearly, feel more confident, second-guess yourself less, and ultimately be more decisive and be more productive?
Making good decisions doesn't have to be a series of endless guesswork. Rather, it's a teachable skill that anyone can sharpen. In How to Decide, bestselling author Annie Duke and former professional poker player lays out a series of tools anyone can use to make better decisions. --- Amazon